Hydrochloric Acid → HCID 56631443, compound

HRID 615681Notes

Reaction equation

HRID 615681 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-:18].[K+].Cl>O>[C:9]([NH:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][S:5][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14797Potassium HydroxideHCID 60960Cysteine Hydrochloride

Product 1

HCID 56631443HCID 56631443, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

63.0 g (0.4 mole) of cysteine hydrochloride were suspended in 400 ml of water, and 112.5 g (0.8 mole) of benzoyl chloride were added. A solution of 89.8 g (1.6 moles) of potassium hydroxide in 1 liter of water was added dropwise to the stirred mixture, while cooling at 0°-5° C. Stirring was continued for a further hour at room temperature, after which the mixture was rendered strongly acidic with aqueous 2N HCl, the precipitate was filtered off under suction and washed neutral with water, and the product was recrystallized twice from methanol/water. 106.3 g (81%) of N,S-dibenzoylcysteine of melting point 183°-185° C. were obtained; Rf=0.43 in system I, [α]D20 =-85.7° (c=1 in absolute ethanol).

Workup

  1. temperaturewhile cooling at 0°-5° C
  2. waitwas continued for a further hour at room temperature
  3. filtrationthe precipitate was filtered off under suction
  4. washwashed neutral with water
  5. customthe product was recrystallized twice from methanol/water

Sources & evidence

ORD record
ord-7ec61ab9b27849efa7feb15f3e356e7a
Source dataset
uspto-grants-1985_02
Patent number
US04500467

Reaction notes

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